2-Chlorobenzyl chloride → HCID 86673393, compound

HRID 1023362Notes

Reaction equation

HRID 1023362 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][N:10]=1.[Cl:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28]Cl.[H-].[Na+]>CN(C=O)C>[CH2:21]([O:20][C:18](=[O:19])/[CH:17]=[CH:16]/[C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:28][C:27]3[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=3[Cl:25])=[CH:11][N:10]=2)=[C:2]([F:1])[CH:3]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 67328977HCID 67328977, compound

Product 1

HCID 86673393HCID 86673393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (40 mL) solution of butyl (E)-3-{3-fluoro-4-[(5-hydroxypyridin-2-yl)oxy]phenyl}prop-2-enoate (3.82 g) and 2-chlorobenzyl chloride (1.6 mL) was added sodium hydride (60% w/w in oil, 0.60 g) at 0° C., and stirred at room temperature for 3 hours. The reaction mixture was quenched by addition of saturated NH4Cl (90 mL), and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl, dried over anhydrous Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=19/1 to 9/1) to afford (E)-3-[4-({5-[(2-Chlorobenzyl)oxy]pyridin-2-yl}oxy)-3-fluorophenyl]prop-2-enoic acid butyl ester (3.53 g).

Workup

  1. customThe reaction mixture was quenched by addition of saturated NH4Cl (90 mL)
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with water, saturated aqueous NaCl
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=19/1 to 9/1)

Sources & evidence

ORD record
ord-c71b5f08e7934f708256a7d1e4ee0ab1
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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